Article
Chemistry, Organic
Xuewei Wang, Yongli Zhao, Jinhua Yang, Yanxi Li, Ying Luo, Mengyao Xu, Junfeng Zhao
Summary: A novel strategy for thioester synthesis using ynamide was developed, showing no detectable racemization for thioesterifications of carboxylic acids with alpha-chiral centers. The method is compatible with amino acid side chain functional groups and can also be used for selenoesters.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Changliu Wang, Chunyu Han, Jinhua Yang, Zhenjia Zhang, Yongli Zhao, Junfeng Zhao
Summary: This study describes an environmentally friendly synthesis of thioamides and primary thioamides using a simple and mild reaction conditions and readily available NaSH as the sulfur source. The reaction can tolerate a wide range of functional groups and maintains the stereochemical integrity of alpha-chiral monothiocarboxylic acids, offering a racemization-free strategy for peptide C-terminal modification. Additionally, this method can be used to prepare thioamide-modified drugs and backbone thiazolyl modified peptides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Silin Xu, Dandan Jiang, Zejun Peng, Long Hu, Tao Liu, Lili Zhao, Junfeng Zhao
Summary: This article presents a systematic mechanistic analysis of ynamide-mediated peptide bond formation and its application expansion. The study finds that ynamide exhibits superiority in addressing the issue of racemization/epimerization during peptide bond formation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Multidisciplinary Sciences
Mohana Reddy Mutra, Jeh-Jeng Wang
Summary: This paper presents a method for the cleavage, migration, and functionalization of C(sp)-N bonds in ynamides under blue LED light without the use of metals or additives. This method has important implications in the synthesis of specific compounds.
NATURE COMMUNICATIONS
(2022)
Review
Chemistry, Organic
Zhao Yongli, Tu Yongliang, Cai Mingzhong, Zhao Junfeng
Summary: Ynamides are a class of special ynamines with an electron-withdrawing group on the nitrogen atom, which have been widely used in organic synthetic chemistry. The recent advances in the synthesis of ynamides and their representative mechanisms are reviewed in this article, classified by the main starting materials including haloenamides, alkynes or its derivatives, and dihalo-substituted alkenes.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Junqi Su, Aobo Chen, Guofeng Zhang, Ziyu Jiang, Jiannan Zhao
Summary: A practical and effective method for synthesizing thioesters from readily available carboxylic acids and odorless disulfides under photocatalytic conditions was developed. This method involves phosphoranyl radical-mediated fragmentation to generate acyl radicals and incorporates both sulfur atoms of the disulfides into the desired products. In addition to batch reactions, a continuous-flow reactor was utilized for rapid gram-scale thioester synthesis. Preliminary experimental mechanistic studies and the rapid synthesis of dalcetrapib were also demonstrated.
Review
Chemistry, Multidisciplinary
Shubham Dutta, Rajendra K. Mallick, Akhila K. Sahoo
Summary: The use of ynamides in organic synthesis has attracted significant attention for their ability to access complex molecular structures through 1,2-difunctionalization and annulation reactions. This review provides a systematic overview of regioselective difunctionalization and annulation reactions of ynamides, including multi-component reactions, radical-triggered functionalizations, and the use of bifunctional reagents. Mechanistic breakthroughs and future prospects of ynamides as versatile building blocks are also discussed.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Tsukasa Tawatari, Ritsuki Kato, Riku Kudo, Kiyosei Takasu, Hiroshi Takikawa
Summary: In this study, we report on the intramolecular (3+2) cycloaddition reactions between ynamides and benzyne. These reactions involve the formation of two bonds and are facilitated by using benzyne precursors containing a chlorosilyl group. The intermediate indolium ylide in these reactions exhibits both nucleophilic and electrophilic properties at its C2 atom.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Xiao-Tong Lin, Cheng Zhao, Da-Ru Wang, Guang-Cheng Wu, Guo-Shu Chen, Shu-Jie Chen, Hai Ren, Dong-Sheng Deng, Yi-Bing Xu, Xiao-Wei Hu, Yun-Lin Liu
Summary: This study presented a BiCl3-mediated tandem cyclization reaction of tryptamine-ynamides, leading to the formation of pentacyclic spiroindoline scaffolds in moderate to excellent yields. The reaction also demonstrated the divergent synthesis of tricyclic indole derivatives with moderate yields by manipulating substrate structures, showcasing the synthetic utility of the methodology.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Engineering, Chemical
Zhefan Zhang, Lingchao Cai, Liangliang Song
Summary: Peptide modification is an important topic in academia and the pharmaceutical industry, with a focus on the diversification of amines, thiols, and alcohols. However, the direct and chemoselective modification of acid residues in peptides is relatively underdeveloped. In this study, a novel and efficient method for the direct functionalization of acid residues in peptides is reported, using ynamides as reaction partners. This approach shows excellent chemoselectivity and a broad scope for various dipeptides containing unprotected Trp or Tyr residue and free Ser or Gln residue.
Article
Chemistry, Multidisciplinary
Lu Yang, Hui Zhou, Yuwei Duan, Meizi Wu, Kun He, Yong Li, Dongfang Xu, Hong Zou, Shaoming Yang, Zhimin Fang, Shengzhong Liu, Zhike Liu
Summary: Judicious tailoring of the SnO2/perovskite interface using DL-dimer passivation can significantly improve the efficiency and stability of perovskite solar cells. The DL-dimer provides better passivation of defects in both the SnO2 and perovskite films, resulting in improved quality of the perovskite film. The DL-treated device achieves an impressive V-OC of 1.20V and a PCE of 25.24%, which is a record value among all reported PSCs.
ADVANCED MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Pierre Hansjacob, Frederic R. Leroux, Morgan Donnard
Summary: The research reports a fully selective Zn-catalyzed hydrocyanation of ynamides, allowing the synthesis of various trisubstituted E-alpha-enamidonitriles. The catalyst-free photoisomerization results in the energetically comparable Z-stereoisomer. Furthermore, the synthetic potential of these newly synthesized alpha-enamidonitriles is evaluated through the synthesis of original heterocycles.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Physical
A. Salam
Summary: The problem of resonance energy transfer between chiral molecules mediated by electrically polarizable bridging particles is solved using molecular quantum electrodynamics theory. Different couplings are employed for donor and acceptor, and the transfer rates are studied for oriented and isotropic systems. Discriminatory transfer rates are observed when certain conditions are met, and the contribution of mixed electric dipole-quadrupole coupling in the fluid phase is found to vanish.
JOURNAL OF CHEMICAL PHYSICS
(2022)
Article
Chemistry, Multidisciplinary
Changwei Chen, Hongyu Zhang, Gang Xu, Sunliang Cui
Summary: This study demonstrates the oxoarylation of ynamides with N-aryl hydroxamic acids, and probes the mechanism and scalability through deuterium-labelling reaction and gram-scale reaction.
CHINESE CHEMICAL LETTERS
(2021)
Article
Environmental Sciences
Sarah Grace Zetterholm, Luke Gurtowski, Jesse L. Roberts, Sheila McLeod, Brianna M. Fernando, Chris S. Griggs
Summary: This study evaluated the interactions of chitosan/graphene composites with different species of cyanobacteria and their impact on water quality. The results showed that the composites were effective in removing algal density and toxins, especially the MC toxins produced by Microcystis aeruginosa.
Article
Chemistry, Organic
Jinhua Yang, Changliu Wang, Chaochao Yao, Chunqiu Chen, Yafang Hu, Guifeng He, Junfeng Zhao
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Changming You, Zhenming Zhang, Yongliang Tu, Hong Tang, Yuanfeng Wang, Da Long, Junfeng Zhao
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Physical
Ming Yang, Xuewei Wang, Junfeng Zhao
Article
Chemistry, Organic
Zhenming Zhang, Bei Fu, Hui Wang, Han Chen, Yongliang Tu, Junfeng Zhao
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Chaochao Yao, Jinhua Yang, Xiaobiao Lu, Shuyu Zhang, Junfeng Zhao
Article
Chemistry, Multidisciplinary
Yongliang Tu, Junfeng Zhao
Summary: Arylhydrazines and quaternary ammonium salts have shown versatile reactivity in Pd-catalyzed coupling reactions, acting as aryl or alkyl donors. Various coupling reactions involving different reaction partners and mechanistic elucidations have been summarized, providing important insights for future research.
Article
Chemistry, Multidisciplinary
Zhengning Wang, Xuewei Wang, Penghui Wang, Junfeng Zhao
Summary: Allenone has been identified as a highly effective peptide coupling reagent for the first time, showcasing its robustness in forming peptide bonds. It is not only effective for synthesizing simple amides and dipeptides, but also suitable for peptide fragment condensation and solid-phase peptide synthesis (SPPS). This method represents a disruptive innovation in peptide synthesis by combining the advantages of conventional active esters and coupling reagents while overcoming their disadvantages.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Chemistry, Organic
Zhao Yongli, Tu Yongliang, Cai Mingzhong, Zhao Junfeng
Summary: Ynamides are a class of special ynamines with an electron-withdrawing group on the nitrogen atom, which have been widely used in organic synthetic chemistry. The recent advances in the synthesis of ynamides and their representative mechanisms are reviewed in this article, classified by the main starting materials including haloenamides, alkynes or its derivatives, and dihalo-substituted alkenes.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xuewei Wang, Yongli Zhao, Jinhua Yang, Yanxi Li, Ying Luo, Mengyao Xu, Junfeng Zhao
Summary: A novel strategy for thioester synthesis using ynamide was developed, showing no detectable racemization for thioesterifications of carboxylic acids with alpha-chiral centers. The method is compatible with amino acid side chain functional groups and can also be used for selenoesters.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Changliu Wang, Chunyu Han, Jinhua Yang, Zhenjia Zhang, Yongli Zhao, Junfeng Zhao
Summary: This study describes an environmentally friendly synthesis of thioamides and primary thioamides using a simple and mild reaction conditions and readily available NaSH as the sulfur source. The reaction can tolerate a wide range of functional groups and maintains the stereochemical integrity of alpha-chiral monothiocarboxylic acids, offering a racemization-free strategy for peptide C-terminal modification. Additionally, this method can be used to prepare thioamide-modified drugs and backbone thiazolyl modified peptides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zhenming Zhang, Bei Fu, Xiaoshuo Wang, Zhipeng Hu, Xuanling Liu, Tao Wang, Junfeng Zhao
Summary: An efficient and general base-promoted reaction for the synthesis of (Z)-beta-chloro-enamides using 1,1-dichloroalkenes and secondary sulfonamides or amides has been described. This reaction exhibits excellent functional group tolerance under simple and mild conditions. Mechanistic study suggests that the stereoselective trans-hydroamidation of alkynyl chlorides generated in situ from 1,1-dichloroalkenes is the key step.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Tao Liu, Xue Zhang, Zejun Peng, Junfeng Zhao
Summary: The novel ynamide coupling reagent allows removal of by-products by water, facilitating direct coupling reactions between carboxylic acids and amines, alcohols, or thiols to produce amides, peptides, esters, and thioesters. The reactions do not exhibit detectable racemization, and a simple acidic aqueous work-up enables the attainment of pure products with good yields. The water-removable ynamide coupling reagent has been successfully demonstrated in the synthesis of carfilzomib without the need for column chromatography purification.
Article
Chemistry, Organic
Tao Liu, Silin Xu, Junfeng Zhao
Summary: Coupling reagents can promote the direct condensation of carboxylic acids with amines or alcohols to form amide or ester bonds, widely used in drug, material, and cosmetic production. However, issues such as impurities and racemization caused by over activation of traditional coupling reagents, as well as large chemical waste from solid phase peptide synthesis, call for new reagents and mechanisms to address them.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Kai Wang, Chenghao Jiang, Zhenming Zhang, Chunyu Han, Xuewei Wang, Yaping Li, Kaiting Chen, Junfeng Zhao
CHEMICAL COMMUNICATIONS
(2020)
